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[ CAS No. 17754-90-4 ] {[proInfo.proName]}

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Chemical Structure| 17754-90-4
Chemical Structure| 17754-90-4
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Product Citations

Product Citations

Raaginie Tamil Segaran ; Chean Hui Ng ; Mohd Fadhlizil Fasihi Mohd Aluwi , et al. DOI:

Abstract: The synthesis of prenylated or geranylated acylphloroglucinol-based xanthenones with 15.1-36.9% yield was achieved via aldol condensation of 2,4,6-trihydroxy-3-prenylacetophenone (tHPA) or 2,4,6-trihydroxy-3-geranylacetophenone (tHGA) and 2-hydroxybenzaldehyde derivatives in the presence of lithium bis(trimethylsilyl)amide (LiHMDS) as deprotonating agent. This study is one of the first to report on the synthesis of xanthenones using strong non-nucleophilic base catalyst, and the described synthesis not only achieved a compound with a natural product skeleton but also formed in a simple and environmentally friendly specificity.

Keywords: Acylphloroglucinol-based xanthenone ; LiHMDS base catalyst ; Aldol condensation ; Natural product skeleton ; Eco-friendly

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Product Details of [ 17754-90-4 ]

CAS No. :17754-90-4 MDL No. :MFCD00003326
Formula : C11H15NO2 Boiling Point : -
Linear Structure Formula :(OH)C6H3(CHO)N(C2H5)2 InChI Key :XFVZSRRZZNLWBW-UHFFFAOYSA-N
M.W : 193.24 Pubchem ID :87293
Synonyms :

Calculated chemistry of [ 17754-90-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.67
TPSA : 40.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 1.75
Log Po/w (WLOGP) : 2.05
Log Po/w (MLOGP) : 1.42
Log Po/w (SILICOS-IT) : 1.8
Consensus Log Po/w : 1.76

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.19
Solubility : 1.24 mg/ml ; 0.0064 mol/l
Class : Soluble
Log S (Ali) : -2.22
Solubility : 1.17 mg/ml ; 0.00605 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.69
Solubility : 0.39 mg/ml ; 0.00202 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 17754-90-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17754-90-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 17754-90-4 ]
  • Downstream synthetic route of [ 17754-90-4 ]

[ 17754-90-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 68-12-2 ]
  • [ 91-68-9 ]
  • [ 17754-90-4 ]
YieldReaction ConditionsOperation in experiment
80% at 5 - 75℃; for 4 h; Phosphorous oxychloride (POCl3) (2.75 ml, 0.03 mol) was slowly added to N,N dimethyl formamide (DMF) (3.65 mL,0.05 mol) at 5–10 °C under constant stirring. To this cooled reagent 3-(N,N-diethyl amino) phenol (0.01 mmol) in DMF(6 mL) was added slowly under constant stirring and the resulting mixture was heated at 75 °C for 4 h. The reaction mixture was cooled to room temperature and then poured into ice cold water (60 mL). The reaction mass was neutralized with sodium carbonate, brown colored solid separated out.The solid product was filtered and washed with cold water,dried and crystallised from ethanol to obtain the pure product 2, Yield =80 percent, m.p. 62 °C (lit. 62 °C)
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 12, p. 2575 - 2584
[2] Journal of Fluorescence, 2015, vol. 25, # 6, p. 1615 - 1628
[3] Chemical Communications, 2016, vol. 52, # 60, p. 9434 - 9437
[4] Chemistry Letters, 2011, vol. 40, # 3, p. 279 - 281
[5] Patent: US2789125, 1953, ,
[6] Journal of Fluorescence, 2012, vol. 22, # 1, p. 311 - 322
[7] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4449 - 4461
[8] Journal of the American Chemical Society, 2017, vol. 139, # 8, p. 3181 - 3185
[9] Patent: CN106749142, 2017, A, . Location in patent: Paragraph 0026; 0027
[10] Organic Letters, 2017, vol. 19, # 1, p. 82 - 85
[11] Patent: US2789125, 1953, ,
  • 2
  • [ 93109-27-4 ]
  • [ 17754-90-4 ]
YieldReaction ConditionsOperation in experiment
95% With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5 h; Inert atmosphere Under the protection of nitrogen, palladium acetate (3.4 mg, 0 . 015 mmol, 5 mol percent) and sodium hydride (60percent in oil, 18 mg, 0.45 mmol, 1.5 equiv) suspension for DMA (1.0 ml), 25 °C stirring 5 minutes, the compound is added 21 (0.3 mmol) in DMA (0.5 ml) solution, then in 50 °C reaction 5 hours, adding ice water stopped reaction, dilute hydrochloric acid for adjusting the pH value to 3.5, extracted with ethyl acetate, the combined extract, sulfate to dry, dry [...], column chromatography purification, to obtain the product 22, yield 95percent.
Reference: [1] ACS Catalysis, 2018, vol. 8, # 4, p. 3016 - 3020
[2] Patent: CN108358760, 2018, A, . Location in patent: Paragraph 0044
  • 3
  • [ 333303-27-8 ]
  • [ 17754-90-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2000, vol. 37, # 6, p. 1447 - 1455
  • 4
  • [ 57489-51-7 ]
  • [ 17754-90-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2000, vol. 37, # 6, p. 1447 - 1455
  • 5
  • [ 591-27-5 ]
  • [ 17754-90-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4449 - 4461
  • 6
  • [ 17754-90-4 ]
  • [ 74-88-4 ]
  • [ 55586-68-0 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With potassium carbonate; potassium hydroxide In acetonitrile at 80℃; for 0.166667 h;
Stage #2: at 80℃; for 2 h;
A mixture of 4-diethylamino-2-hydroxy benzaldehyde (5.8 g,30 mmol), KOH (2 g, 35 mol) and K2CO3 (8.3 g, 60 mmol) inacetonitrile (30 ml) was heated for 10 min at 80 °C. MeI (3.5 ml,56 mmol) was added to this alkaline mixture and stirring wascontinued for another 2 h at 80 °C. The reaction mixture was thencooled to room temperature filtered. The filtrate was concentratedunder reduced pressure and chromatographed on silica gel column(mesh sizee120-200) eluting with EtOAc/hexane in 1:3 ratio to get pure compound as yellow solid (yield 85percent).1H NMR (500 MHz, CDCl3) δ 10.11 (s, 1H), 7.68 (dd, J 8.9, 2.8 Hz,1H), 6.26 (d, J 8.8 Hz, 1H), 6.02 (s, 1H), 3.87 (s, 3H), 3.41 (dd,J 6.9, 2.7 Hz, 4H), 1.21 (t, J 5.4 Hz, 6H).13C NMR (125 MHz, CDCl3) δ: 187.1, 164.1, 153.8, 130.7, 114.2,104.2, 92.4, 55.2, 44.7, 12.5 (see Fig. 2).
Reference: [1] Journal of Physical Chemistry A, 2004, vol. 108, # 31, p. 6452 - 6454
[2] Dyes and Pigments, 2018, vol. 148, p. 474 - 491
[3] RSC Advances, 2013, vol. 3, # 46, p. 24021 - 24024
[4] Patent: US2017/320846, 2017, A1, . Location in patent: Sheet 16
  • 7
  • [ 74-83-9 ]
  • [ 17754-90-4 ]
  • [ 55586-68-0 ]
Reference: [1] Dyes and Pigments, 2011, vol. 90, # 1, p. 56 - 64
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